Process for the preparation of 1,2,3,4,8,9,10, 10a-octahydro-7bH-cyclopenta[b][1,4]diazepino-[6,7,1-hi]indole derivatives

Abstract

This invention provides processes for preparing compounds formula: wherein R is H, alkyl, acyl, aryl, aroyl or —C(O)R′; R′ is alkyl or aryl; R 1 , R 2 , R 4 and R 5 are H, —OH, alkyl, cycloalkyl, alkoxy, halogen, fluorinated alkyl or alkoxy, —CN, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, acyl, aryl or aroyl; R 3 is H, alkyl, cycloalkyl, alkoxy, fluorinated alkyl, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, aryl, or aroyl; or a pharmaceutically acceptable salt thereof, as well as novel compounds useful in the synthesis of these compounds.

1. A compound of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 4  and R 5  are each, independently, hydrogen, hydroxy, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, halogen, fluorinated alkyl of from 1 to 6 carbon atoms, —CN, —NH—SO 2 -alkyl of 1-6 carbon atoms, —SO 2 —NH-alkyl of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluorinated alkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl or aroyl. 
     
     
       2. A compound of  claim 1  wherein R 1  and R 2  are hydrogen, and R 4  and R 5  are as defined in  claim 1 . 
     
     
       3. A compound of  claim 1  wherein R 1 , R 2  and R 4  are hydrogen, and R 5  is as defined in  claim 1 . 
     
     
       4. A compound of  claim 1  which is 2-(2,3,3a,8b-Tetrahydro-1H-cyclopenta[b]indol-4-yl)-acetamide. 
     
     
       5. A compound of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 4  and R 5  are each, independently, hydrogen, hydroxy, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, halogen, fluorinated alkyl of from 1 to 6 carbon atoms, —CN, —NH—SO 2 -alkyl of 1-6 carbon atoms, —SO 2 —NH-alkyl of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluorinated alkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl or aroyl. 
     
     
       6. A compound of  claim 5  wherein R 1  and R 2  are hydrogen, and R 4  and R 5  are as defined in  claim 1 . 
     
     
       7. A compound of  claim 5  wherein R 1 , R 2  and R 4  are hydrogen, and R 5  is as defined in  claim 1 . 
     
     
       8. A compound of  claim 5  which is 2-(2,3,3a,8b-Tetrahydro-1H-cyclopenta[b]indol-4-yl)-acetonitrile. 
     
     
       9. A compound of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 4  and R 5  are each, independently, hydrogen, hydroxy, alkyl of 1-6 carbon atoms, cycloalkyl, alkoxy of 1-6 carbon atoms, halogen, fluorinated alkyl of from 1 to 6 carbon atoms, —CN, —NH—SO 2 -alkyl of 1-6 carbon atoms, —SO 2 —NH-alkyl of 1-6 carbon atoms, alkyl amide of 1-6 carbon atoms, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl moiety, fluorinated alkoxy of 1-6 carbon atoms, acyl of 2-7 carbon atoms, aryl or aroyl. 
     
     
       10. A compound of  claim 9  wherein R 1  and R 2  are hydrogen, and R 4  and R 5  are as defined in  claim 1 . 
     
     
       11. A compound of  claim 9  wherein R 1 , R 2  and R 4  are hydrogen, and R 5  is as defined in  claim 1 . 
     
     
       12. A compound of  claim 9  which is 2-(2,3,3a,8b-Tetrahydro-1H-cyclopenta[b]indol-4-yl)-ethylamine.